PdI2-catalyzed coupling-cyclization reactions involving two different 2,3-Allenols:: An efficient synthesis of 4-(1′,3′-Dien-2′-yl)-2,5-dihydrofuran derivatives

被引：35

作者：

Deng, Youqian ^{[1
]}

Li, Jing ^{[1
]}

Ma, Shengming ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Zhejiang, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 14期

关键词：

alcohols; allenes; cyclization; elimination; palladium;

D O I：

10.1002/chem.200800167

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Transition-metal-catalyzed dimeric coupling-cyclization reactions of two different 2,3-allenols afforded 4-(1',3'-dien-2'-yl)-2,5-dihydrofuran derivatives 3. 2-Substituted 2,3-allenols I cyclized to form the 2,5-dihydrofuran ring, whereas the 2-unsubstituted 2,3-allenols 2 provided the 1,3-diene unit at the 4-position. The reaction is proposed to proceed through an oxypalladation, insertion, and P-hydroxide elimination process. The C=C double bond was formed with high E stereoselectivity by beta-hydroxide elimination.

引用

页码：4263 / 4266

页数：4

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